
Holiday home rentals near Chesapeake Bay
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Top-rated holiday home rentals near Chesapeake Bay
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1 BDRM Beaut-5 min walk to Metro/10 min from DC
Whether you are traveling for work or pleasure, look no further than this centrally located 1-bedroom/1-bath apartment, just minutes and perfectly located from DC's museums, monuments, & more! This metro accessible, luxuriously decorated apartment can accommodate your every need while in our beautiful city. Travel with ease & take advantage of a fully equipped kitchen, fast WIFI and during downtime, step outside to enjoy a relaxing evening in the shared space under the gazebo with a fire pit!

Stunning one-bedroom private suite
Hi I'm a professional software engineer and a proud father of 3 beautiful children. I'm optimistic, and cheerful, and love communicating with others. Having just started hosting, excited to be a part of this community and to be able to help people feel right at home. Being an explorer myself, I find it really enlightening to discover new places and learn about local cultures. It would be my pleasure to have you as a guest on my new build property and ensure that you have a pleasant stay with me.

Down By The Bay - Cape Charles -1st Floor Primary
🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 1st floor Primary bed 2026, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June - August

Northern Neck Waterfront
Relax with the whole family at this peaceful waterfront retreat. Nestled along Coles Creek and the Great Wicomico River, this 3-bedroom house is a perfect waterfront getaway with all the amenities you need for a comfortable stay. Savor the beauty of nature from our backyard, where a glistening pool takes center stage, inviting you to unwind and bask in the sun. If you're an aquatic enthusiast or simply someone in search of serenity, our house in Burgess offers an idyllic haven to vacation.

Tranquil Beachfront Getaway on the Chesapeake Bay!
Recharge your battery and reset your mind by staying at our waterfront paradise. Spend time with your tribe while relaxing in this beautiful, well appointed home featuring stunning wide water views of the Chesapeake Bay. "Almost Heaven" is located at the end of a gravel lane, amongst trees, making it the perfect getaway. The expansive patio and beachfront yard offer infinity views of your private beach. Bait a crab pot to catch your own dinner or enjoy a meal from one of the local restaurants.

Serene Cozy Couples Getaway
Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

In-Law Suite in Van Ness/Cleveland Prk/free parkin
Bright new in-law suite with a separate entrance, full kitchen, washer & dryer, fast internet, pull-out couch, laptop desks, and a pack n' play for little ones. Easy access to National Mall via Van Ness metro stop four minutes away. Flexible check in and check out, no cleaning fees (though smoking, marijuana and incense are a firm no). We've been hosting people from all over the world for several years, and we're happy to help you have a great time in Washington, for leisure or work!

Waterfront 5 Bedroom Home Close to Annapolis
Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Stylish Farmhouse - porch, firepit
Beautiful rural farmhouse with stylish decor and a lovely front porch overlooking a serene field. This homey space is chic and elegant with a modern kitchen, bath and amenities. Step outside for a 2 mile wooded walk/bike ride to a tiny secluded BEACH. Watch the stars from the front porch, grill outside, fire pit, or chill out with ROKU tv. Modern plus old-fashioned gives you a nostalgic, stylish, and comfortable rural getaway. Great central base for exploring the entire Shore!

Spacious Garden Apartment on Delightful Street
This delightful apartment is on the ground floor of a large single family house in a charming neighborhood, just 2 blocks from the center of Takoma Park, a 15 minute walk to the Metro. With its open floor plan, you will enjoy the large living room and windowed alcove, a fully-equipped kitchen, dining room and ample-sized bedroom with wall-to-wall closets. There is a separate entrance and laundry room. The house has a large front yard, with shade trees and nice gardens.

Waterfront 4 bedroom home with marina facilities
Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

One Bedroom Guest Studio Suite
Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.
Popular amenities for holiday home rentals near Chesapeake Bay
Family-friendly holiday home rentals

Charming Beach/Bay Escape with Activities for All!

VB Paradise / Private Pool, Hot Tub

Fun and Sun in Ocean View! 5 bedrooms 12 guests

New Hot Tub, Patio, Pet-Friendly-2blocks to all!

Downtown Bay View Luxury Condo Spectacular view!

Cheerful 3 bedroom home with a pool and sauna

Solo/Couple's Escape in Sandbridge, Virginia Beach

Vacay Stay-2BR/1Bath, Family Groups Only
Holiday home rentals with a patio

Luxurious 5 Bedroom Near Beach, Amenities Galore!

Sunset Bay homestay

Peace & Tranquile waterfront home

The Observatory on Rose Manor

Beach Happy-steps to the beach- 4bedrooms/9guest

Private Close to Everything One-Bedroom Apartment

Parkside South, Cape Charles

Lovely 2-bedroom 1100 sq ft Apt with free parking
Holiday home rentals with a washing machine and dryer

1 Block to the Beach, Indoor Pool Great 4 Kids

Beautiful Waterfront Home

Sara's Cottage

Harbor View - 3 bedroom home in the heart of town.

Bright 3 bedroom vacation home near beach

Relaxing 3-Bedroom Beach Cottage By Historic Lewes

Hoopers Island 4BR Waterfront • Sunset Views

Harvest of tranquillity
Other holiday home rentals

House near Crystal City, Pentagon, Amazon &Museums

Home Away from Home Condo with pool

Ocean Beach Club 3 Bedroom Penthouse- City View

Rancher central to all the fun! Fenced Yard, Deck

Lovely 2-bdrm home/ Please book 3 week in advance

Quaint vacation home in historic Williamsburg

Private basement/Stafford Va

Beautiful 1 BR Apt. Great HomeAway & business trip
Destinations to explore
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- Holiday home rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




